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Stuart was drafted in the first round, 3rd overall, in the 1998 NHL Entry Draft by the San Jose Sharks. In a game against the Los Angeles Kings on April 4, 2004, Stuart scored twice in a 17-second span, forcing the game into overtime at a 3-3 tie. The San Jose Sharks went on to win 4-3. Stuart's feat is the fastest that a Sharks player has scored two goals only behind Owen Nolan's two goals 8 seconds apart during the 1997 NHL All-Star game.

Stuart was an unrestricted free agent after the 2007–08 season and on July 1, 2008, he re-signed with the Detroit Red Wings for $15 million over 4 years.[4] Stuart returned to his home town of Rocky Mountain House on August 17, 2008 with the Stanley Cup to share his celebration with those that supported him.

Stuart played in 67 games during the 2008–09 season, scoring two goals to go with 13 assists as the Red Wings came within one game of repeating as Stanley Cup Champions.

On June 10, 2012, Stuart's negotiating rights were traded to the San Jose Sharks in exchange for the negotiating rights to forward Andrew Murray and a conditional 7th round pick in the 2014 NHL Entry Draft.[5] Eight days later, it was reported that Stuart signed a three-year $10.8 Million deal with the Sharks.[6] In the 2013–14 season on October 8, 2013 against the New York Rangers, Stuart recorded a hit on Rick Nash which led to Stuart being suspended for three games.[7] He finished the season with 11 points in 61 games before surrendering a 3-0 series lead in the Conference Quarterfinals to the Los Angeles Kings.

On July 1, 2014, with the Sharks intent on getting younger, Stuart accepted a trade to provide a veteran presence to the Colorado Avalanche in exchange for a 2nd round draft pick in 2016 and a 6th round pick in 2017.[8] Before playing a game with the Avalanche prior to the 2014–15 season, Stuart was signed to a two-year contract extension on September 29, 2014.[9] Stuart played in his 1,000th career game on December 18, 2014.[10]